Acetic Acid → HCID 23329129, compound

HRID 225161Notes

Reaction equation

HRID 225161 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:14])[CH2:9][CH2:10][C:11]([OH:13])=[O:12])=[CH:4][C:3]=1[S:15](=[O:18])(=[O:17])[NH2:16].[C:19](Cl)(=O)C.C(O)(=O)C.C(=O)(O)[O-].[Na+]>CO.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:14])[CH2:9][CH2:10][C:11]([O:13][CH3:19])=[O:12])=[CH:4][C:3]=1[S:15](=[O:17])(=[O:18])[NH2:16]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 6367Acetyl chlorideHCID 516892Sodium BicarbonateHCID 23329118HCID 23329118, compound

Product 1

HCID 23329129HCID 23329129, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

27 g of 4-(4-chloro-3-sulfamoylphenyl)-4-oxobutanoic acid are dissolved in 200 ml of methanol, 1 g of acetyl chloride is added and the mixture is stirred at room temperature. After 24 hours, only small amounts of starting material can still be detected in the thin layer chromatogram. The solvent is driven off, the residue is treated with 200 ml of acetic acid/200 ml of water and, after the pH has been adjusted to 8 with saturated sodium bicarbonate solution, the mixture is stirred vigorously for 30 minutes. After separating off the organic phase and drying it over sodium sulfate, the solvent is distilled off and methyl 4-(4-chloro-3-sulfamoylphenyl)-4-oxobutanoate is obtained.

Workup

  1. stirringthe mixture is stirred vigorously for 30 minutes
  2. customAfter separating off the organic phase
  3. dry with materialdrying it over sodium sulfate
  4. distillationthe solvent is distilled off

Sources & evidence

ORD record
ord-2999b8cc7da641d6b9a2fff3857dbb33
Source dataset
uspto-grants-1980_11
Patent number
US04235918

Reaction notes

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